👋 Hi Reader,

Hope you're having an amazing start to your weekend! Here's what's included in today's newsletter:

• 📧 Open enrollment, investments & more listener Q&A
• 💺 Business class award deals to 8 destinations
• 🏥 My wife's preventative surgery updates
• 🔗 Card-linked offers worth $1,000+ in savings
• 🥗 Free $40 from InKind for new and existing users
• 💵 Up to $1,000 investment account bonus
• 🛫 3 easy ways to earn bonus miles via airline promos
• 🍔 Play McDonald's Monopoly for free and more!

If you enjoyed reading this, please feel free to forward it to anyone else who might (and if that's you, you can subscribe here). Thank you!

Chris

📧 Open Enrollment, Investments & More Listener Q&A

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This week on the podcast, I answered lots of your questions covering open enrollment, investing, buying gold, life and auto insurance, RSUs, practical ways to leverage AI tools, and more.

Thanks to everyone who submitted questions. I've already recorded a few more AMAs to answer other questions, but if you have a question you'd like to submit for a future AMA, please share it here.

And if you want to go deeper on health insurance and open enrollment, check out this episode from last year:

📋 My Past Week

Let me share a quick recap of what I was up to last week:

• After 4 years of having an incredibly loud garage door, I had a garage door installer come out to see what we could do. Turns out a quick 30-min service made all the difference and it feels like we just installed a brand new quiet garage door. I can't believe it took us this long to do this, but I'm so glad we did.
• I'm trying hard to use a few AI coding tools to turn my Credit Card Optimizer Spreadsheet Tool into an app, but all the different credit card earnings rules I’ve added make it way more complex than I had realized. So it looks like it'll be a much bigger project than I originally thought, but stay tuned!
• I was looking forward to earning some points paying our taxes, but when we finally got our 2024 return filed last week (thanks Gelt) we ended up having a small refund. Maybe next year!
• Finally, my wife Amy has the BRCA2 gene mutation and had surgery two days ago to preventatively remove her ovaries and significantly reduce her risk of ovarian cancer. Everything went great and she's recovering at home right now. Hopefully she has a quick recovery like she did last year after a double mastectomy she did for the same reason. For those not familiar, more than 60% of women with BRCA2 develop breast cancer during their lifetime. Being proactive can make a huge difference, and I'm so proud of my wife for going through all this!

🛫 Travel, Points & Miles

🏨 Hotel Promos: Marriott, Hilton, Accor & Best Western

Here are some of the hotel promos to take advantage of if you have upcoming travel plans.

• Best Western: Earn 1,000 bonus points per night on up to 10 nights. Register here, book, and complete the stay before 11/2.
• Marriott: Earn 2,025 bonus points per stay (up to 3 stays) this fall, plus 2K extra for stays at Outdoors locations. Register here and book before 12/27 for stays between 10/28 and 1/10/26.
• Hilton: Save 25% on Asia-Pacific stays between 10/24 and 3/31/26.
• Accor: Earn 2x points on 2+ night stays across the Americas between 10/15 and 3/31/26. Register here and book before 1/15/26. You can also save up to 30% at select North American properties when booked by 3/30/30 for stays between 10/15 and 3/31/26. The discount is progressive, where you get 10% off for 1-2 nights, 15% off for 3-4 nights and 20% off for 5+ nights.

💺 Business Class Award Deals to 8 Destinations

Check out these business class award flight deals if you're looking to travel to/via these destinations.

• 🇦🇺 Australia: From 85K AAdvantage miles
• 🇭🇰 Hong Kong: First-class from 160K Cathay Pacific Asia miles
• 🇮🇪 Ireland: From 45K Atmos points
• 🇮🇹 Italy: From 55K Atmos points
• 🇳🇱 Netherlands: From 48.5K Virgin points
• 🇰🇷 South Korea: From 75K Atmos points
• 🇪🇸 Spain: From 40.5K Avios points
• 🇬🇧 UK: From 23K Virgin points

If you're not set on business class, Singapore Airlines' Spontaneous Escapes promo is offering 30% off saver awards to multiple destinations that are listed here when you book before 10/31.

🛫 3 Easy Ways to Earn Bonus Miles via Airline Promos

Airline promos like these are relatively easy ways to earn bonus points.

• United: Earn extra miles via the Mile Play promo. Register here before 12/22 and enter your MileagePlus loyalty number to see your targeted offer.
• Southwest: Earn 1K bonus points when you spend $100 via the Southwest Rapid Rewards Shopping portal before 10/20.
• TAP Portugal: Earn 50% bonus on miles when you book any flight before 10/20 with promo code BDAY2025USD.

🤩 Rove's Loyalty Eligible Hotel Bookings (10x Miles)

Rove Miles is a really interesting hotel booking platform that lets you earn their own transferrable points currency when booking hotels. However most hotel booking sites aren't eligible for earning points or elite nights with hotel chains. Fortunately, Rove just announced that you will be able to book hotel rates that earn points and elite status, making it a really compelling platform for booking hotels.

Plus, through 10/31, you can earn 10x Rove Miles per $1 spent on eligible bookings at hotels including Hyatt, Marriott, Hilton, IHG, and more. This is exciting news considering Rove Miles can be transferred to 12 different hotel and airline partners.

💸 2x Rewards (Up to 6% Back) on Venmo Credit Card

A targeted offer is allowing select Venmo Credit Card holders to earn double rewards through December, meaning 6% back on your top category, 4% on the next category, and 2% everywhere else. Check your Venmo app to see if you're eligible and activate the offer.

🤑 Latest Deals

🥗 Free $40 InKind Dining Credit (New & Existing Users)

InKind is a dining rewards app that's helped me save $100s at some amazing restaurants and they're continuing to offer more deals. Right now, new and existing customers can get $15 off $15 and $25 off $50. Plus, if you don’t have an InKind account yet, you can join with a $25 off $50​ referral offer first (here’s mine) and then active the offers above.

P.S. If you split the bill with others, you can both use these deals.

💵 Up to $1,000 Bonus for BoA Merrill Edge Investments

If you're a Bank of America Preferred Rewards member, you can get up to a $1,000 bonus when you invest in a new Merrill Edge Self‑Directed account using promo code 1000PR. You need to maintain the balance for 90 days, but you can transfer existing investments over without needing to sell them.

🔗 Card-Linked Offers: $1,000+ in Savings

Here are some card-linked offers I found this week with expiration dates in parentheses. Also, note that some of these offers are targeted, so I recommend using CardPointers Pro (get 30% off here) to automate these offers.

• AT&T Fiber: $50 off $75 (11/8)
• Wyndham: $40 off $200 (12/5)
• Miraval Resorts & Spas: $70 off $700 (12/8)
• Big Sky Resort: $500 off $2,000 (12/25)
• Lyft: 10% back, up to $10 (12/31)
• Qatar Airways: $200 off $850+ (12/31)
• Virgin Atlantic: $250 off $1,800 (12/31)
• Hilton: 20,000 bonus points after a $10K spend or 6,000 bonus points after a $3K spend on Amex Hilton cards (2/10/26)

🛒 $35-$60 Off Sam’s Club Memberships

Through 10/31, new members can join Sam’s Club for just $15 (normally $50) or upgrade to a Plus membership for $50 (normally $110). This offer is not valid for renewals, members who canceled in the past 6 months or guest members.

⛽ Save 25¢ per Gallon Every Friday with Amazon Prime

Amazon Prime members can save 25¢ per gallon every Friday at bp, Amoco and am/pm gas stations in the U.S. through 12/26. All you need to do is activate the offer ​here​ and create a free account with BP.

📦 $10 Off $50 Walmart Delivery Purchases

Get $10 off an order of $50+ at Walmart when you use promo code DOUBLE10. It seems to only work on delivery orders, but you can use this offer up to 2 times.

💰 Aeroplan, Flying Blue, EVA Air & More Points on Sale

Do you have a redemption in mind, or are you familiar with these programs? Check out these deals with expiration dates in parentheses.

• Aeroplan: 1.4¢ with up to a 90% bonus (10/29)
• Flying Blue (Targeted): 1.69¢ with up to a 45% bonus (11/5)
• EVA Air: 0.2¢ with up to a 50% bonus (11/20)
• Marriott Bonvoy: 0.89¢ with up to a 40% bonus (12/7)

💬 Parting Thoughts

As always, thanks so much for reading! I didn't get to include everything I normally do, because my priority this week was my wife and the kids! But if you have suggestions for a future newsletter, please share them by replying to this email. Thanks!

Chris